Does this happen a lot? I got a corrected 1099 last year in like March after I'd already filed and it was a huge pain to amend my return.

Yes, it happens quite frequently. Late corrections are especially common with complex investments like REITs, MLPs, and certain mutual funds that have to wait for information from underlying investments. The later in February they release your original forms, the less likely you'll get a correction. March corrections usually come from very complex securities or from issuers who discovered reporting errors after the fact. That's why many tax professionals actually advise clients with investment income to wait until early March to file, just to avoid the amendment headache.

Crypto exchanges are usually faster than traditional brokerages. I got my Coinbase tax forms around January 25th last year. The reason is they don't have to deal with many of the issues mentioned above like wash sale rules (which don't technically apply to crypto yet) or corrected information from third parties.

3 That's brutal! So even though they call it a "tuition" prize, you could still end up owing a huge tax bill? Do they at least warn contestants about this before they participate?

10 From what I've read, most of these contests don't really emphasize the potential tax implications in their marketing materials or rules. They might include some fine print that "winner is responsible for all applicable taxes," but contestants often don't realize how significant that can be until they receive the 1099. The smart winners usually consult with a tax professional immediately after winning to structure how they receive and use the funds. Some have reportedly negotiated to have the money sent directly to their educational institution over multiple years to maximize the potential for scholarship treatment. But yes, many winners have been caught off guard by the tax implications of these "tuition" prizes.

17 That's really helpful insider info! So if I ever win something like this, I should specifically request that the money be sent directly to my school rather than to me personally? Would that make a difference in how it's taxed?

So what about if there's a real business conference and I bring my kid who works for my business? Is any part of that deductible or is it all considered personal?

If there's a legitimate business conference and your child who legitimately works for your business has a valid business reason to attend, then their expenses related to the conference itself would be deductible as a business expense. This includes their registration, their portion of the hotel room during the conference dates, and their meals while attending business activities. However, if you extend the trip for sightseeing or vacation activities, those additional days would not be deductible. And any activities that are clearly personal in nature (like visiting tourist attractions or entertainment) wouldn't be deductible either, even during the business portion of the trip. The IRS looks at the primary purpose of each expense.

Your kids would only have to file taxes if their income exceeds the standard deduction (which is $13,850 for 2025). So if they make less than that, they typically don't have to file a federal return. But you still need to keep proper payroll records, issue them a W-2, and follow all employment laws.

Did you use any specific tracking system for this? I've got options from 3 different employers and I'm worried about keeping everything straight.

I actually created a simple spreadsheet where I track each grant separately. I have columns for grant date, exercise date, number of shares, strike price, FMV at exercise, exercise cost, bargain element, AMT paid, sale date, sale price, and gain/loss for both regular tax and AMT purposes. I also keep a digital folder with all the PDF statements and confirmations, named with the date and transaction type. This system saved me during my audit because I could immediately show the IRS exactly where my calculations came from. There are also specialized software options for this, but honestly, a well-organized spreadsheet has worked perfectly for my situation.

That strategy can work but you lose the potential for LTCG treatment. If you exercise and sell in the same year, the entire gain is treated as ordinary income. So you avoid AMT but potentially pay more in regular tax. It really depends on how much the stock has appreciated and what your regular income is. For my situation with a startup that had 5x growth, it was actually better to take the AMT hit and then get LTCG treatment a year later, even considering the time value of money. Run the numbers both ways!

Thanks for the explanation. Makes sense about losing the LTCG treatment. I guess I need to look at how much the stock might appreciate versus the extra tax cost. My company is still pretty early stage, so holding for LTCG might be worth the AMT complications if we keep growing.

They don't currently get any stipend or per diem for the travel unfortunately. That's why we're trying to figure out if there's any tax relief available. The union does have some provisions for travel pay, but only for jobs beyond a certain distance (I think it's 75 miles), and most of their assignments fall just under that threshold. Do you know if there's a standard mileage rate they could use instead of tracking actual gas costs?

Yes, using the standard mileage rate is usually much easier than tracking actual gas expenses. For 2024, the standard mileage rate for business travel is 67 cents per mile. This covers gas, wear and tear, depreciation, and insurance. If your partner qualifies to deduct these expenses (based on the temporary work location rules others mentioned), using the standard rate is typically much simpler than keeping all gas receipts. Just make sure they keep a detailed log of dates, locations, business purpose, and miles driven. There are several good mileage tracker apps that can help with this too.

This is the correct answer that everyone else missed. The Tax Cuts and Jobs Act suspended miscellaneous itemized deductions subject to the 2% floor from 2018 through 2025. This includes unreimbursed employee business expenses like mileage to job sites. If they're a W-2 employee, these expenses aren't deductible at the federal level right now. Some states still allow these deductions on state returns though, so check your state tax laws!